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Reactivity of (Z)-4-arylidene-5(4H)-oxazolones: [4+2] cycloaddition versus [4+3] cycloaddition/nucleophilic trapping

✍ Scribed by Alberto Avenoza; Jesús H. Busto; Carlos Cativiela; Jesús M. Peregrina

Publisher: Elsevier Science
Year: 2002
Tongue: French
Weight: 136 KB
Volume: 43
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(02)00744-x

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✦ Synopsis

The use of different aluminum derivatives in the reaction between cyclopentadiene and (Z)-2-phenyl-4-arylidene-5(4H)oxazolones, and in particular the use of different equivalents of the reagent, allows the modulation of the synthesis of the norbornane skeleton by a [4+2] cycloaddition or the more interesting bicyclo[3.2.1]octane framework by a [4+3] cycloaddition followed by nucleophilic trapping of the ionic dipole cycloadduct with cyclopentadiene.

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